Life: Taking a Chance

It’s been a little over a month since my last life update, so let’s catch up on what’s happening.

I’m Moving Back to Portland

It’s true, I’ve decided to move back to Portland. There are some wonderful people (and opportunities) in the Bay, but I’m just not a fan of the area, for reasons I’ve touched on in the past. I’ve spent a lot of the past month deciding what to do next and where, and one thing I settled on pretty early was that whatever I did next, it wouldn’t be here. (All that said, I finally had the time to get out and see more of Berkeley and Oakland, and it’s definitely grown on me in ways that SF and the peninsula never did.)

As I was deciding where to be, an opportunity came up in Portland for a room in a house with good people for a reasonable rate: the timing couldn’t be better, so I took the hint and made the decision to move back to Portland — for at least the next 6-9 months, but probably longer.

Picking My Path

I mentioned last time that I was debating four options. I did some soul searching, and conversations with family and friends about it all, and things kept on landing on option 4: do my own thing. It’s risky: it’s easy to end up in the weeds, and hard to make a living. But it’s also where my endgame has always been: the whole point of working for others was to save enough money that I could do what I wanted without having to constantly worry about making rent.

I don’t have that magical retirement fund, but that’s okay. I can afford to float for a little while, and it seems dumb to put off being and doing what I actually want to do just because I’m feeling risk-averse.

So that’s what I’m doing. I’m going to spend the summer learning, experimenting, figuring out what I can do to make things work. In the fall, we’ll see what ideas seem to have legs and are worth pursuing. If things still haven’t started to bear fruit by when my finances hit my “oh shit” threshold, I’ll start figuring out other options (jobs, grad school, etc). (While it’s certainly possible to hit the ground running and start making money with early work, it feels naively optimistic to assume that will be the case, so I’m not putting that as an objective for the summer. If opportunity knocks, neat.)

Sometimes the right answer, for your own happiness and wellbeing, is to take a chance.

What I’m Focusing On

There are a few specific areas that I want to explore this summer, that all scratch different itches (there’s a theme underpinning all of them, though):

  1. Small Software: I’m not out to create empires or build a huge business. There are, however, some pieces of software that I wish existed, that I feel like are within my potential to build. Small, targeted projects (hopefully) done well.
  2. Writing: Fiction and non-fiction. I want to get back to writing, and I have some ideas I’ve been meaning to explore for a long time.
  3. Arts & Crafts: I’ve got literally years of “oh man, that should be a t-shirt/bumper sticker/pin” ideas that I’d like to start, y’know, actually making instead of just idly saying they should be made. There’s also various other art projects (photography mostly) that I want to do.

What Else is New?

I finally got to see people in the Bay! Go figure, it’s as I’m planning to leave, but that doesn’t change that it’s been nice to do. I caught up with my friend Tim, whom I’ve known since high school. He’s always been good people, and it was great to see him and find out what he’s been up to.

I also finally got to connect with my friend Nina, whom I’d mostly known from Twitter (other than a brief meeting at the first XOXO). She’s super rad, and has definitely helped me get out and enjoy more of the area. (She just started a new gig working on Project Jacquard — super excited to see what she creates!)

I also was able to connect with other friends, spending time with my friend Chris, and seeing Mime, Anaid, Eric, and others, along with stopping by the new Dropbox offices and seeing friends there, like Angie and Sy. I’d say I’ve gotten to see and spend time with more people now that I’m leaving than I did in the months leading up to it. It’s felt good to have some social connection.

I’d be lying if I said I wasn’t nervous about what the coming year will hold, but I’m also excited by its potential. I’m going to do my best to keep the blog up to date with how things are going (along with the random links and quotes I like the share, and maybe even some other writing), so stay tuned!


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